Agree, shoot for a computerized telescope at $500 or less. In Plano, while there will be light pollution, the things that he's going to want to be looking at are all bright, and you can see them wherever (moon, planets, bright stars). Even the Orion nebula will be bright enough to see.
The only people who really need scopes in the +$1000 to +$10,000 range are those who want to be able to view a large variety of objects, including dark sky objects, as well as photograph them easily and well.
If you want to get into Astrophotography, I would start with a DSLR camera, wide angle lens (Milky Way) or super telephoto (Moon) on a sturdy tripod first before you ever move to shooting through a telescope.
There are also really cool gadgets and accessories out there to where you can photo the sun and moon very easily with your phone, i.e.
Hestia from Vaonis.
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